Adipoyl chloride → HCID 13004485, compound

HRID 1995853Notes

Reaction equation

HRID 1995853 reaction equation
[N:1]([CH:4]([CH2:7][N:8]=[N+:9]=[N-:10])[CH2:5][OH:6])=[N+:2]=[N-:3].[C:11](Cl)(=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>C(Cl)(Cl)(Cl)Cl>[N:1]([CH:4]([CH2:7][N:8]=[N+:9]=[N-:10])[CH2:5][O:6][C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[CH2:7][N:8]=[N+:9]=[N-:10])=[O:17])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 61034Adipoyl chlorideHCID 12916747HCID 12916747, compound

Product 1

HCID 13004485HCID 13004485, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

8.52 g (0.06 Mole) 2,3-diazidopropanol in 20-ml dry CCl4 is added dropwise to 5.49 g (0.03 Moles) adipyl chloride in 30-ml dry CCl4 while the temperature is held below 20° C. At the end of the addition, the cooling bath is removed and the temperature is allowed to rise to 25° C. The reaction mixture is allowed to stir at ambient temperature for 18 hours under a slow flow of nitrogen to purge HCl produced in the reaction. At the end of this period the reaction mixture is washed with H2O, dilute bicarbonate solution, and a final H2O wash. The resultant colorless solution is stripped of solvent to yield 9.8 g (83%) colorless oil nD25 1.5050, d425 1.258; infrared spectrum is consistent with the expected structure. Elemental analysis for nitrogen gives 42.01%, theoretical is 42.62%.

Workup

  1. customis held below 20° C
  2. additionAt the end of the addition
  3. customthe cooling bath is removed
  4. customto rise to 25° C
  5. customto purge HCl
  6. customproduced in the reaction
  7. washAt the end of this period the reaction mixture is washed with H2O, dilute bicarbonate solution
  8. washa final H2O wash

Sources & evidence

ORD record
ord-5f3abda603794921ae14b8f95006bd84
Source dataset
uspto-grants-1983_09
Patent number
US04406718

Reaction notes

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